Dicyclohexylcarbodiimide → HCID 20076277, compound

HRID 704287Notes

Reaction equation

HRID 704287 reaction equation
[C:1]([C:3]1([CH2:10][CH2:11][CH3:12])[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1)#[N:2].O1[C:17]2([CH2:22]CC(=O)[CH2:19][CH2:18]2)OCC1.S(C[N+]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[Li+].CC([N-]C(C)C)C.C(Br)CCCCCC.[BH4-].[Na+].[CH2:55]([CH:59]1[CH2:64][CH2:63][CH:62]([CH:65]2[CH2:70][CH2:69][CH:68]([C:71]([OH:73])=O)[CH2:67][CH2:66]2)[CH2:61][CH2:60]1)[CH2:56][CH2:57][CH3:58].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([C:3]1([CH2:10][CH2:11][CH2:12][CH2:22][CH2:17][CH2:18][CH3:19])[CH2:4][CH2:5][CH:6]([O:9][C:71]([CH:68]2[CH2:67][CH2:66][CH:65]([CH:62]3[CH2:61][CH2:60][CH:59]([CH2:55][CH2:56][CH2:57][CH3:58])[CH2:64][CH2:63]3)[CH2:70][CH2:69]2)=[O:73])[CH2:7][CH2:8]1)#[N:2]

Participants

11

Reactant 8

HCID 10868DicyclohexylcarbodiimideHCID 123691-BromoheptaneHCID 161915Tosylmethyl isocyanideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 17121624'-Butyl-1,1'-bi(cyclohexyl)-4-carboxylic acidHCID 2724682Lithium diisopropylamideHCID 4311764Sodium borohydrideHCID 1981943199568-13-5

Product 1

HCID 20076277HCID 20076277, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1 g of 4-dimethylaminopyridine and 22.3 g (0.1 mole) of 4-cyano-4-propylcyclohexanol (isomer mixture) [obtainable from 1,4-dioxaspiro[4,5]decan-8-one by introduction of the nitrile group with tosylmethyl isocyanide, alkylation with LDA and n-heptyl bromide, detachment of the keto-protective group and reduction of the ketone with NaBH4 ] are added to 26.6 g (0.1 mole) of 4'-butylbicyclohexane-4-carboxylic acid in 75 ml of CH2Cl2, with stirring. A solution of 21.7 g (0.105 mole) of dicyclohexylcarbodiimide in 50 ml of CH2Cl2 is added dropwise, while controlling the temperature, and the mixture is then stirred at room temperature for a further hour. The urea precipitated is separated off and the methylene chloride phase is washed with dilute HCl and saturated NaHCO3 solution and dried. After the solvent has been evaporated off, the residue is separated into its constituents by column chromatography (silica gel/petroleum ether (30-70):ether (5:1)). 4-(4-Cyano- 4-heptylcyclohexyloxycarbonyl)-4'-butylbicyclohexane is obtained.

Workup

  1. stirringthe mixture is then stirred at room temperature for a further hour
  2. customThe urea precipitated
  3. customis separated off
  4. washthe methylene chloride phase is washed with dilute HCl and saturated NaHCO3 solution
  5. customdried
  6. customAfter the solvent has been evaporated off
  7. customthe residue is separated into its constituents by column chromatography (silica gel/petroleum ether (30-70):ether (5:1))

Sources & evidence

ORD record
ord-856f72d7254447e0b20c60c1fcb71910
Source dataset
uspto-grants-1991_01
Patent number
US04985583

Reaction notes

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